Conventionally, a 3,3′,4,4′-biphenyltetracarboxylic acid and a 3,3′,4,4′-biphenyltetracarboxylic dianhydride thereof, which may be produced by dehalogenative coupling of a halogenated phthalic acid (see, for example, Patent Literature 1) or oxidation of methyl group of a 3,3′,4,4′-tetramethylbiphenyl (s-TMBP) (see, for example, Patent Literature 2), are widely known as a starting material for a polyimide.
As a method for producing the 3,3′,4,4′-tetramethylbiphenyl (s-TMBP), a method comprising a step of dimerizing o-xylene using a Grignard reagent in the presence of copper chloride to produce s-TMBP, for example, is disclosed (see, for example, Patent Literature 3). Furthermore, a method comprising a step of dimerizing o-xylene in the presence of palladium bis(trifluoroacetate), copper acetate, and pyridine-2-carboxylic acid to produce TMBP (a mixture of s-TMBP and a-TMBP (2,3,3′,4′-tetramethylbiphenyl)), particularly with a-TMBP selectivity of 70 mol % or more (production ratio of s-TMBP (s/a)=30/70 or less) is disclosed (see, for example, Patent Literature 4).
Meanwhile, as a method for producing a compound having a cyclohexylbenzene skeleton, a method comprising a step of reacting benzene with hydrogen in the presence of a catalyst for producing cyclohexylbenzene, which contains a hydrogenation catalyst comprising a mesoporous material as a support, and a solid acid catalyst modified with a metal of Group 2 or Group 3, to produce cyclohexylbenzene, for example, is disclosed (see, for example, Patent Literature 5).